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His father is musician, like his brothers Walter, Wallie and Johnnie. Soon after his birth the family moved to St. Louis, after a few years again to return to Arkansas.Roosevelt grew up in the West Helena district, where he plays organ in the Church at a young age. He teaches himself to play piano and runs like 12-year-old away from home to go to work in barrelhouses and gambling houses of West Helena.
In 1929 he began making recordings. First for the Okeh label and later as supervisor of various blues singers for various labels in Chicago and Cincinnati. He used various pseudonyms as The Blues Man, Easy Papa Johnson, Willie Kelly, Dobey Bragg (his mother's maiden name) and the name by which he would become best known: The Honeydripper. Allegedly he had this name due to the enormous success he has with the other gender.
Chicago offers him many opportunities, so he settles in the Windy City. Between 1937 and 1941 , he works as a talent scout for Decca Records and travels a lot by the USA, along with St. Louis Jimmy. His fame as a blues pianist is a much sought-after accompanist he is ever expanding, for other artists, and is on many recordings to hear.